Potassium Iodide → 1-[2-(Diphenylmethoxy) ethyl]-3-(3-methoxyphenyl)pyrrolidine

HRID 1032335Notes

Reaction equation

HRID 1032335 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][CH2:9][CH2:10]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]2[CH2:30][CH2:29][NH:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][CH2:9][CH2:10][N:28]2[CH2:29][CH2:30][CH:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH3:18])[CH:21]=3)[CH2:27]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 237821[(2-Bromoethoxy)(phenyl)methyl]benzeneHCID 129379913-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 145563061-[2-(Diphenylmethoxy) ethyl]-3-(3-methoxyphenyl)pyrrolidineYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 17.5 g (60 mmole) of 1-(diphenylmethoxy)-2-bromoethane in 50 cm3 of dimethylformamide was added to a mixture of 10.6 g (60 mmole) of 3-(3-methoxyphenyl)pyrrolidine [prepared according to A. Ebnother and K. Hasspacher, Swiss Patent No. 526 536], 16.6 g (120 mmole) of potassium carbonate, 300 cm3 of dimethylformamide and a few potassium iodide crystals. The mixture was heated at 80° C. for 13 hours, and concentrated to dryness under reduced pressure after it returned to room temperature. The residue was taken up with 500 cm3 of 1N hydrochloric acid and extracted with ether. The aqueous acid phase was separated, basified with 10N sodium hydroxide solution, and extracted with methylene chloride. The organic solution was dried on sodium sulfate. The evaporation of the solvent provided an oily residue. Purification by silica gel filtration (eluent, hexane-ethyl acetate, 1/1) yielded 10 g of 1-[2-(diphenylmethoxy) ethyl]-3-(3-methoxyphenyl)pyrrolidine, which was dissolved in 100 cm3 of ether. To this solution was added a solution of 2.55 g (28.3 mmole) of oxalic acid in 30 cm3 of acetone. The oxalate precipitate was filtered and recrystallized from acetone.

Workup

  1. customprepared
  2. concentrationconcentrated to dryness under reduced pressure after it
  3. customreturned to room temperature
  4. extractionextracted with ether
  5. customThe aqueous acid phase was separated
  6. extractionextracted with methylene chloride
  7. customThe organic solution was dried on sodium sulfate
  8. customThe evaporation of the solvent
  9. customprovided an oily residue
  10. customPurification
  11. filtrationby silica gel filtration (eluent, hexane-ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-fa2074557a68440f834e73daeec32ecc
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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